“Desai is a long time Google employee, first joining the company in 2003. He’s currently their Director of Product Management and has led development of product/businesses in Google’s advertising business (including AdWords, Syndication & TV Ads).”

I’m watching CNN on a Virgin America flight from JFK to SFO, and the lead story (at 10:25am Eastern) is the of a cargo plane near Shanghai that killed all 3 Americans on board. At the next break, the second commercial is for British Airways — a spot built around China’s Canton Fair, a 3-week event at which (according to the voice-over) $2 billion dollars a day trade hands.

For years I’ve been asked by marketers how I’ll protect their brands if they run ads on blogs that allow comments or sites like Digg, where readers select the stories that get promoted to the homepage. My answer has always been: The same way CNN does it. “If, god forbid, there’s a plane crash, CNN must cover the story. So someone in CNN’s traffic department immediately pulls all airline advertisers out of rotation until that news cycle passes.” While humans are still better than algorithms at avoiding (or recovering from) these kinds of awkward associations, the CNN approach — as I just witnessed — remains an imperfect system.

Do I now need to find a new example with which to answer that question, or should I just point out that those uncomfortable situations you fear will happen online are also happening on TV?

I love the UPS-sponsored , a dashboard of business news. The site is built by PopURLs on top of the site’s system of filtering and aggregating web content. What I love even more than the PopURLs Brown Edition destination site: All of the site’s value is syndicated into ad units, like these on Guy Kawasaki’s Alltop. I don’t need to click on the banners to appreciate the value UPS is bringing to me.

A study by Comscore, AOL’s Tacoda and Starcom back in February 2008 showed that 50% of all clicks on banner ads were done by just 6% of Internet users. A repeat of the study, published in October 2009, shows the core group of heavy clickers (8% now) are responsible for 85% of ad clicks.

And these “natural born clickers” are not the most desirable demographic for most advertisers: They skew toward Internet users with household incomes below $40,000 who spend more time than average at gambling sites and career advice sites.

Digg’s lead scientist, Anton Kast, recently shared with me an analysis of who’s clicking on Digg Ads, the ads on Digg that give readers the option of Digging and burying them like regular Digg stories. Since advertisers buy Digg Ads on a cost-per-click basis, I was eager to see the results.

Instead of concentrated click activity by a small group of (inexplicably) click-happy individuals, clicks on Digg Ads (red line) are spread across a wide population of light clickers. In other words, the branded content items promoted by Digg Ads units is appealing to lots of people, each of whom clicks on an occasional ad. The profile of these Digg Ads clickers roughly matches Digg’s upscale demographic, unlike the “natural born clickers.”

Digg Ads (still in beta) doesn’t yet offer much targeting, so relevance can’t entirely explain these better results. Digg Ads do, however, offer advertisers an opportunity to speak to Digg readers in the “local vernacular” of Digg — blue headlines that point to content next to yellow boxes with numbers in them, and the option to Digg and bury the sponsored content just like organic content stories on the site. Kind of like the paid search ads on Google results pages, which I bet have a diversity of clickers that goes well beyond the “natural born clickers” too.

Targeting (relevance) is great. But finding ad formats that are native to content experiences may be just as important.

In other words, more people are doing something with the content they read (commenting, sharing, voting), but they’re doing it on the large social platforms like Facebook, Twitter and Digg rather than in the comments fields on the sites where the content originates.

From the piece on Digg’s platform, as well as ad systems on Reddit, Facebook and others that allow readers to voice real-time feedback on the advertising.

“The Internet has long provided a measurement of how effective an ad is — that is how many times it was clicked versus how often it was shown, a metric called click-through rate. But that’s based simply on how loud and flashy a banner can be in order to attract a reader’s attention.

“A click doesn’t necessarily convert to a purchase, or ‘conversion’ as they call it, nor are visitors guaranteed to associate the product positively. If an ad mimics a virus alert, it might get clicked out of fear or urgency but won’t elicit a pleasant reaction once users realize they were duped.”

Exactly. Click-through rate is a blunt instrument and neglects the quality of those clicks. A dozen clicks by high-value customers who want to engage with your brand, product offers or retail partners are much more valuable than a hundred clicks by individuals who came to win a free Harley and forgot who’s offering that Harley.

“Conversion rate” (for retail advertisers), “time spent” and “share volume” are a few other metrics that are at least as important as CTR. “Quality score” should be another, since low quality will affect all the others. Advertisers running Digg Ads here at Digg, for example, get more exposure and lower rates based not only on CTR but by the ratio of Diggs (positive feedback) to buries (negative feedback). While CTR rewards the urgency of the offer and the relevance of the advertising copy, Diggs and buries — votes which tend be submitted after a Digg reader clicks on an ad — measure the totality of the experience. Did the landing page deliver what the ad promised? Was the experience on the advertiser’s site a good one? Was it good enough that you’d share it with a friend or a few thousand followers in Twitter?

Get your customers to click, but remember that the click is only the first date.

“Filing a patent application, of course, doesn’t necessarily mean that the company plans to use the technology. But the application shows, at the least, that Apple has invested in research to develop what it calls an ‘enforcement routine’ that makes people watch ads they may not want to watch.

“Its distinctive feature is a design that doesn’t simply invite a user to pay attention to an ad — it also compels attention. The technology can freeze the device until the user clicks a button or answers a test question to demonstrate that he or she has dutifully noticed the commercial message. Because this technology would be embedded in the innermost core of the device, the ads could appear on the screen at any time, no matter what one is doing.”

Nobody does product placement better than 30 Rock. Instead of taking the money and quietly hiding the product on set, 30 Rock leans in — hard. In the latest episode, Alec Baldwin’s Jack Donaghy is required by circumstances to video conference, and the show’s writers take it over the top by working in lines that make Jack sound like he’s reading from the Cisco TelePresence brochure.

The lost opportunity (for Cisco and for NBC) is that the product-placement scene is locked up at Hulu. You can watch it there by scrolling through the episode, but it would reach many more eyeballs if fans could excerpt the clip and set free on YouTube.

Driving down the Santa Monica Freeway in LA yesterday I got my first look at Toyota’s floral billboard for Prius, which went live (literally) back in August:

“Toyota’s partnership with Greenroad Media of Santa Monica includes the upkeep of nine urban freeway sections, which basically consists of maintaining and repairing corresponding irrigation and landscape in exchange for using the ground as a floral billboard. Caltrans does not allow any product identification in the actual floral designs, but a nearby sign with the Prius name proudly displayed is installed nearby.”

Some press gave Toyota a hard time for making advertising that requires watering. I don’t get that — we all love gardens and flowers and parks, all of which require watering. So as long a flower billboard is pretty like non-advertising gardens, where’s the problem? Plus I’ve got to believe that replacing metal-plastic-and-ink billboards (with flood lights pointed at them) with plant-based billboards would be a net positive for the environment.